1. Field of the Invention
The present invention relates to a cosmetic composition suitable for sensitive skin, dry skin, roughening skin or skin with atopic dermatitis, comprising an N-long chain acylamino acid or a salt thereof, which composition is excellent in foam breakage and feeling after its use.
2. Description of the Background Art
Inorganic salts and organic salts of N-long chain acylamino acids have bactericidal activity in addition to surface activity. Cleansing agents comprising these salts are mild to skin and have an excellent detergency, and thus are widely used as a main component of cleansing compositions (Japanese Published Examined Patent Application No. 38604/79, Japanese Published Examined Patent Application No. 83538/93 and Japanese Published Examined Patent Application No. 27720/85).
Among the salts of N-long chain acylamino acids used as cleansing agents, salts of N-long chain acylamino acids of a tertiary amide type are excellent in water-solubility, but are known to have the defects that much rinse is necessary for breaking the foam generated and that they give a slimy feeling. Salts of N-long chain acylamino acids of a secondary amide type are known to have disadvantages that the foam is not stable enough for cleansing and that they give a poor feeling after their use. To solve these problems, it is known to use an N-long chain acyldipeptide in combination with an N-long chain acylamino acid (Japanese Published Unexamined Patent Application No. 78693/93).
An N-acylglutamine is known to have hair-growing activity (Japanese Published Unexamined Patent Application No. 32726/94), melanin formation inhibiting activity (Japanese Published Unexamined Patent Application No. 157284/94) and cleansing activity (WO 97/03171).
Recently, the number of persons with sensitive skin, dry skin, roughening skin or the like, and that of patients with atopic dermatitis caused by allergic reaction or the like, have been remarkably increased. In persons with sensitive skin, dry skin, roughening skin or the like, or in patients with atopic dermatitis, the use of general cosmetics sometimes causes strong irritative feelings since their skins have become to be hypersensitive. Also, there is a possibility that surfactants or the like contained in cosmetics, soaps or the like may aggravate dermatitis in these persons or patients due to damaged cellular surfaces of their skins. Thus, development of low-irritative cosmetics, particularly those having a cleansing function, which can be used without anxiety even in the persons with sensitive skin, dry skin, roughening skin or the like, or in the patients with atopic dermatitis is demanded.
An object of the present invention is to provide a cosmetic composition having effects suitable for sensitive skin, dry skin, roughening skin or skin with atopic dermatitis.
The present invention relates to the following (1) through (15).
(1) A cosmetic composition comprising one or more compounds selected from N-long chain acylamino acids represented by formula (I): 
xe2x80x83wherein n represents 1 or 2, and R represents a saturated or unsaturated hydrocarbon group having 5 to 23 carbon atoms [hereinafter referred to as Compound (I)]; and salts thereof.
(2) A cosmetic composition for skin selected from the group consisting of sensitive skin, dry skin, roughening skin and skin with atopic dermatitis which comprises one or more compounds selected from the N-long chain acylamino acids represented by formula (I) according to (1) as above and salts thereof.
(3) A cosmetic composition for sensitive skin comprising one or more compounds selected from the N-long chain acylamino acids represented by formula (I) according to (1) as above and salts hereof.
(4) A cosmetic composition for dry skin comprising one or more compounds selected from the N-long chain acylamino acids represented by formula (I) according to (1) as above and salts thereof.
(5) A cosmetic composition for roughening skin comprising one or more compounds selected from the N-long chain acylamino acids represented by formula (I) according to (1) as above and salts thereof.
(6) A cosmetic composition for skin with atopic dermatitis comprising one or more compounds selected from the N-long chain acylamino acids represented by formula (I) according to (1) as above and salts thereof.
(7) The cosmetic composition according to any one of (1) to (6) as above, wherein the N-long chain acylamino acid is N-lauroyl glutamine or an N-cocoylglutamine.
(8) The cosmetic composition according to any one of (1) to (7) as above, which has a cleansing function.
(9) A method for improving a condition of skin selected from the group consisting of sensitive skin, dry skin, roughening skin and skin with atopic dermatitis which comprises applying thereto an effective amount of cosmetic composition according to any one of (1) to (8) as above.
(10) A method for improving a condition of sensitive skin which comprises applying thereto an effective amount of cosmetic composition according to any one of (1) to (8) as above.
(11) A method for improving a condition of dry skin which comprises applying thereto an effective amount of cosmetic composition according to any one of (1) to (8) as above.
(12) A method for improving roughening skin which comprises applying thereto an effective amount of cosmetic composition according to any one of (1) to (8) as above.
(13) A method for improving a condition of skin with atopic dermatitis which comprises applying thereto an effective amount of cosmetic composition according to any one of (1) to (8) as above.
(14) A method of use of the cosmetic composition according to any one of (1) to (8) as above, wherein the composition is applied on skin selected from the group consisting of sensitive skin, dry skin, roughening skin and skin with atopic dermatitis.
(15) A method for treating skin selected from the group consisting of sensitive skin, dry skin, roughening skin and skin with atopic dermatitis comprising applying thereto a cosmetic composition according to any one of (1) to (8) as above.
In the definitions of the groups in Compound (I), examples of the saturated hydrocarbon group having 5 to 23 carbon atoms are straight-chain or branched-chain ones such as pentyl, isopentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl, eicosyl, heneicosyl, docosyl, and tricosyl. Examples of the unsaturated hydrocarbon group having 5 to 23 carbon atoms are straight-chain or branched-chain ones such as pentenyl, 3-methyl-1-butenyl, hexenyl, heptenyl, octenyl, nonenyl, decenyl, undecenyl, dodecenyl, tridecenyl, tetradecenyl, pentadecenyl, hexadecenyl, heptadecenyl, octadecenyl, nonadecenyl, eicosenyl, heneicosenyl, docosenyl, tricosenyl, 1,3-pentadienyl, 8,11-heptadecadienyl, 8,11,14-heptadecatrienyl, and 4,7,10,13-nonadecatetraenyl.
Examples of the salts of Compound (I) are alkali metal salts such as sodium salt, potassium salt, and lithium salt; alkaline earth metal salts such as calcium salt and magnesium salt; ammonium salt; amine addition salts such as salts with monoethanolamine, triethanolamine, and triisopropanolamine; and basic amino acid addition salts such as salts with arginine and lysine. These basic components may be used singly or in combination.
Compound (I) can be prepared by converting a straight-chain or branched-chain fatty acid having 6 to 24 carbon atoms which is saturated or unsaturated (hereinafter referred to as a long chain fatty acid) into a halide such as chloride or bromide by the use of a halogenating agent such as thionyl chloride or phosgene, and then condensing the halide with an amino acid selected from glutamine and asparagine (hereinafter referred to simply as an amino acid). Alternatively, Compound (I) can be prepared by converting a long chain fatty acid into an acid anhydride, and then reacting the acid anhydride with an amino acid.
As the long chain fatty acid, fatty acids composed of single fatty acid such as caproic acid, enanthic acid, caprylic acid, pelargonic acid, capric acid, undecylic acid, lauric acid, tridecylic acid, myristic acid, pentadecylic acid, palmitic acid, stearic acid, isostearic acid, nonadecanoic acid, arachic acid, behenic acid, lignoceric acid, oleic acid, sorbic acid, linolic acid, linolenic acid, and arachidonic acid can be used. Fatty acids composed of more than one fatty acids such as a coconut oil fatty acid and a palm kernel oil fatty acid can also be used as a long chain fatty acid.
A representative process for preparing Compound (I) via an acid halide is described below.
A long chain fatty acid is dispersed in a solvent such as methylene chloride, chloroform, carbon tetrachloride, benzene, toluene, xylene or n-hexane, and 1 to 5 equivalents of a halogenating agent is added thereto based on the long chain fatty acid to obtain a long chain acyl halide as a reaction product. Then, an amino acid is dissolved or dispersed in a solvent, and the above-mentioned long chain acyl halide is added thereto in an amount of 0.3 to 1.0 equivalent based on the amino acid, while maintaining the reaction solution at a temperature of 5 to 70xc2x0 C., and thus acylation is carried out to obtain Compound (I).
Examples of the solvent used for acylation are water, methanol, ethanol, isopropanol, isobutanol, acetone, toluene, tetrahydrofuran, ethyl acetate, N,N-dimethylformamide and dimethyl sulfoxide, which may be used singly or in combination. In the step where an amino acid is dissolved or dispersed in a solvent, an alkaline substance such as sodium hydroxide or potassium hydroxide in an amount of 0.8 to 2.0 equivalents based on the amino acid may also be dissolved or dispersed in the solvent as may be appropriate.
In the case where a salt of Compound (I) is desired and it is produced in the form of the desired salt, it can be subjected to purification as such. In the case where Compound (I) is produced in the free state and its salt is desired, Compound (I) is dissolved or suspended in a suitable solvent, followed by addition of a base to form a salt.
Compound (I) is usually contained in the cosmetic composition of the present invention in an amount of 1 to 90 wt %, preferably 3 to 80 wt %.
The cosmetic composition of the present invention for sensitive skin, dry skin, roughening skin or atopic dermatitis includes any cosmetic composition, by which the conditions of the skin, where sensitive skin, dry skin, roughening skin or atopic dermatitis is caused, are prevented from aggravation or is improved, without strong irritation to the skin.
The above cosmetic composition can be used as skin care products such as face lotion, milk lotion, cosmetic liquid, beauty liquid, cream and pack; make-up cosmetics such as lipstick, foundation, eye shadow, eyeliner and blusher; hair care products such as hair conditioner and hair pack; and cleansing agents, a cosmetic having a function of cleansing skin, hair or the like; including a soap, such as facial wash, body soap, liquid bath soap, hand soap, body rinse, hair shampoo, hair rinse and pack. Among them, the use as a cleansing agent is preferable.
The formulations of the above cleansing agent include solid, paste, powder and liquid forms.
In addition to Compound (I), the cosmetic composition of the present invention can be formulated to contain various ingredients generally used in cosmetics, such as oils and fats, hydrocarbons, waxes, fatty acids, synthetic esters, alcohols, thickeners, moisturizing agents, preservatives, fragrances, dyes, pigments, chemicals, and water.
Examples of the fats and oils are jojoba oil, castor oil, olive oil, soy bean oil, coconut oil, palm oil, cacao butter, mink oil, turtle oil, and coconut oil fatty acid diethanolamide.
Examples of the hydrocarbons are liquid paraffin, vaselline, microcrystalline wax, and squalane.
Examples of the waxes are bee wax, lanolin, carnauba wax and candelilla wax.
Examples of the fatty acids are myristic acid, palmitic acid, stearic acid, oleic acid, and isostearic acid.
Examples of the synthetic esters are isopropyl myristate, isopropyl palmitate, butyl oleate, myristyl myristate, octyldecyl myristate, propylene glycol monostearate, myristyl lactate, isostearyl malate, glycerin monostearate, and distearyldimethylammonium chloride.
Fats and oils, hydrocarbons, waxes, fatty acids and synthetic esters are usually contained in the composition in an amount of 0 to 30 wt % collectively.
Examples of the alcohols are ethanol, 1,3-butylene glycol, propylene glycol, lauryl alcohol, cetanol, stearyl alcohol, and oleyl alcohol. Alcohols are usually contained in the composition in an amount of 0 to 25 wt %.
Examples of the thickeners are carboxyvinyl polymers, methyl polysiloxane, dextran, carboxymethyl cellulose, carrageenan, and hydroxypropylmethyl cellulose. Thickeners are usually contained in the composition in an amount of 0 to 0.5 wt %.
Examples of the moisturizing agents are glycerine, propylene glycol, 1,3-butylene glycol, pyroglutamic acid, acetyl glutamin, hyaluronic acid, and procyanidine. Moisturizing agents are usually contained in the composition in an amount of 0 to 25 wt %.
Examples of the preservatives are benzoic acid, paramethylbenzoic acid, salicylic acid, dehydroacetic acid or salts thereof, phenols such as p-hydroxybenzoates, triclosan, and halocarban. Preservatives are usually contained in the composition in an amount of 0 to 0.3 wt %.
Any fragrances may be used so long as they are usually used in cosmetics.
Any dyes may be used so long as they are usually used in cosmetics.
Examples of the pigments are iron oxide, titanium dioxide, zinc oxide, kaolin and talc. Pigments are usually contained in the composition in an amount of 0 to 1 wt %.
Examples of the chemicals are wheat germ oil, vitamin A, vitamin B2, vitamin E, magnesium ascorbic acid-2-phosphate, sodium ascorbic acid-2-phosphate, D-pantothenyl alcohol, dipotassium glycyrrhizinate, glutathione, UV absorbers, chelating agents, plant extracts, and microbial metabolites/extracts. Chemicals are usually contained in the composition in an amount of 0 to 5 wt %.
Examples of the water are tap water, mineral water, brine water, marine deep water, seawater, ultrapure water, mineral-containing water, and purified water. Water is usually contained in the composition in an amount of 0 to 99 wt % as may be appropriate.
The cosmetic composition of the present invention may take any forms of soluble system, for example, emulsion type, dispersion system, and the like.
The cosmetic composition having a cleansing function may be formulated to contain adjuvants such as solubilizing agents or builders, if necessary, and also surfactants such as anionic surfactants, cationic surfactants, amphoteric surfactants or nonionic surfactants to adjust foaming and detergency.
Examples of the surfactants are fatty acid soap, salt of higher alcohol sulfate, salt of polyoxyethylene higher alcohol sulfate, salt of higher alcohol phosphate, salt of polyoxyethylene higher fatty acid phosphate, salt of sulfonated higher fatty acid, salt of sulfonated higher fatty acid alcohol ester, salt of higher fatty acid isethionate, salt of xcex1-sulfo higher fatty acid ester, higher alkyldimethylbenzylammonium salt, higher alkylamine, higher alkyltrimethylammonium salt, higher fatty acid diethanolamide and its ethylene oxide or propylene oxide addition product, higher fatty acid monoethanolamide and its ethylene oxide or propylene oxide addition product, polyoxyethylene higher fatty acid monoethanolamide phosphate, salt of N-long chain acylamino acid such as salt of N-long chain acyl acidic amino acid, salt of N-long chain acyl sarcosine and salt of N-long chain acyl xcex2-alanine, higher alkylamino propinonate such as laurylamino propionate, higher alkylimino diacetate such as laurylimino diacetate, and amine or amide compounds such as higher alkyldimethyl betaine, higher alkyldihydroxyethyl betaine, salt of N-alkanoyl-Nxe2x80x2-(2-hydroxyethyl)-Nxe2x80x2-carboxymethylethylene-diamine, and N-alkanoyl-N-(2-hydroxyethyl)-Nxe2x80x2,Nxe2x80x2biscarboxymethylethylenediamine.